+ Site Statistics
References:
54,258,434
Abstracts:
29,560,870
PMIDs:
28,072,757
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Expedient stereoselective synthesis of coronafacic acid through intramolecular Diels-Alder cyclization



Expedient stereoselective synthesis of coronafacic acid through intramolecular Diels-Alder cyclization



Journal of Organic Chemistry 72(4): 1235-1240



A stereoselective synthesis of coronafacic acid, a natural component of the phytotoxin coronatin, was achieved using an intramolecular Diels-Alder reaction as the key step. The triene precursor bearing a substituted diene and a vinylketone as dienophile was synthesized and then tested in the thermal intramolecular cyclization. We have devised a new strategy to assemble the E,Z-diene through the stereoselective aldol reaction of an ester enolate followed by a stereoselective dehydration. Following the thermal cyclization, the corresponding hydrindanone thereby obtained with the desired relative stereochemistry could easily be converted into the natural product. The synthesis of the coronafacic acid was accomplished in six steps in 29% overall yield.

Please choose payment method:






(PDF emailed within 0-6 h: $19.90)

Accession: 049016919

Download citation: RISBibTeXText

PMID: 17256906

DOI: 10.1021/jo062099j


Related references

High diastereoselection in the intramolecular diels alder reaction of o quinodimethanes an expedient entry to trans benzoperhydroindans a highly stereoselective total synthesis of racemic estrone and racemic adrenosterone. Journal of the Chemical Society Perkin Transactions I (9): 1639-1646, 1989

Total synthesis of dextro levo coronafacic acid by an intermolecular diels alder approach. Canadian Journal of Chemistry 62(9): 1747-1750, 1984

The synthesis of racemic coronafacic acid by a tandem wessely oxidation diels alder reaction sequence. Journal of the Chemical Society Chemical Communications (10): 739-740, 1990

Synthesis of lachnanthocarpone by intramolecular diels alder cyclization of a 1,7 diarylheptadienoid orthoquinone. Tetrahedron letters: 2 147-150, 1977

Dual behavior of masked o-benzoquinones in intramolecular Diels-Alder reactions. Expedient synthesis of highly functionalized cis-decalins from 2-methoxyphenols. Journal of Organic Chemistry 70(23): 9156-9167, 2005

Stereoselective synthesis of an analog of podophyllotoxin by an intramolecular diels alder reaction. Journal of Organic Chemistry 50(7): 1087-1105, 1985

Lactone-directed intramolecular Diels-Alder cyclization: synthesis of trans-dihydroconfertifolin. Journal of Organic Chemistry 67(13): 4501-4504, 2002

Intramolecular diels alder cyclization of conjugated aldehydes synthesis of a chlorothricolide intermediate. Journal of Organic Chemistry 49(26): 5277-5279, 1984

Stereoselective total synthesis of racemic 3 oxosilphinene through intramolecular diels alder reaction. Journal of the Chemical Society Perkin Transactions I (6): 1331-1338, 1987

A stereoselective synthesis of d normorphinan derivatives by means of an intramolecular diels alder reaction. Chemical & Pharmaceutical Bulletin (Tokyo) 34(12): 4971-4977, 1986

Stereoselective synthesis of the octahydronaphthalene unit of integramycin via an intramolecular Diels-Alder reaction. Organic Letters 7(7): 1355-1358, 2005

Enantiospecific naphthopyran synthesis by intramolecular diels alder cyclization of 4 keto 2 3 unsaturated c glycosides. Tetrahedron Letters 32(9): 1183-1186, 1991

An enantiospecific synthesis of dextro and levo 20 epi ibophyllidine via an intramolecular diels alder type cyclization. Tetrahedron Letters 30(15): 1959-1962, 1989

Total synthesis of (+)-tubelactomicin A. 1. Stereoselective synthesis of the lower-half segment by an intramolecular Diels-Alder approach. Organic Letters 7(11): 2261-2264, 2005

A stereoselective total synthesis of racemic delta 9 12 capnellene via the intramolecular diels alder approach. Journal of the Chemical Society Chemical Communications (9): 646-647, 1991